14 days in Hawaii Itinerary

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Fly
1
Kailua-Kona, Island of Hawaii
— 1 day
Drive
2
Hilo, Island of Hawaii
— 2 nights
Fly
3
Koloa, Kauai
— 2 nights
Fly
4
Kahuku, Oahu
— 2 nights
Drive
5
Honolulu, Oahu
— 7 nights
Fly

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Kailua-Kona, Island of Hawaii — 1 day

Heart of the Kona Coast

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
To see other places to visit, photos, where to stay, and other tourist information, read our Kailua-Kona vacation planning app.

Palm Springs to Kailua-Kona is an approximately 9-hour flight. You'll gain 2 hours traveling from Palm Springs to Kailua-Kona due to the time zone difference. Expect a bit cooler weather when traveling from Palm Springs in May: highs in Kailua-Kona hover around 83°F, while lows dip to 73°F. On the 10th (Wed), you're off to Hilo.
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Outdoors · Tours · Parks · Wildlife
Find places to stay May 10 — 11:

Hilo, Island of Hawaii — 2 nights

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
To find traveler tips, reviews, and tourist information, refer to the Hilo online holiday planner.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in May, you can expect nighttime temperatures to be a bit cooler in Hilo, with lows of 67°F. On the 12th (Fri), you're off to Koloa.
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Outdoors · Tours · Parks · Nature
Find places to stay May 10 — 12:

Koloa, Kauai — 2 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Get ready for a full day of sightseeing on the 14th (Sun): take a tour by water with Boat Tours & Water Sports and then take an unforgettable tour with a helicopter tour.

To find photos, traveler tips, other places to visit, and tourist information, read Koloa trip planner.

You can fly from Hilo to Koloa in 4.5 hours. In May in Koloa, expect temperatures between 82°F during the day and 71°F at night. Finish your sightseeing early on the 14th (Sun) to allow enough time to fly to Kahuku.
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Side Trips
Find places to stay May 12 — 14:

Kahuku, Oahu — 2 nights

Kahuku is a census-designated place (CDP) in the Koolauloa District on the island of Oahu, County of Honolulu, Hawaii, United States. Start off your visit on the 15th (Mon): experience rural life at Kahuku Farms. Get ready for a full day of sightseeing on the 16th (Tue): meet some fierce fish with a shark diving experience.

To see where to stay, other places to visit, ratings, and tourist information, refer to the Kahuku itinerary planning app.

You can fly from Koloa to Kahuku in 2.5 hours. Traveling from Koloa in May, Kahuku is little chillier at night with lows of 65°F. Finish your sightseeing early on the 16th (Tue) to allow enough time to drive to Honolulu.
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Tours · Outdoors · Wildlife
Side Trip
Find places to stay May 14 — 16:

Honolulu, Oahu — 7 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your day by day itinerary now includes Hawaiian Style Cooking Classes, Boat Tours & Water Sports and Helicopter Tours. And it doesn't end there: take a tour by water with Boat Tours & Water Sports, steep yourself in history at Battleship Missouri Memorial, examine the collection at USS Bowfin Submarine Museum & Park, and indulge your taste buds at Food & Drink.

For where to stay, photos, and other tourist information, use the Honolulu travel itinerary planner.

Drive from Kahuku to Honolulu in 1.5 hours. Alternatively, you can take a bus. Traveling from Kahuku in May, expect somewhat warmer with lows of 71°F in Honolulu. You'll have a few hours on the 23rd (Tue) to wrap things up before traveling home.
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Tours · Outdoors · Classes · Wildlife
Find places to stay May 16 — 23:

Hawaii travel guide

4.4
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.
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